Personally, I like to keep mine on a MTM after the initial lease expires because it’s more advantageous for the landlord and I can raise the rent more often than once per year if needed.

Initially, we won't be making any cash flow for the first year which we're okay with but after that we plan to rent it out to start the cash flow process (we're doing our due diligence by doing the calculations and using rentometer to make sure our rental income would offset our mortgage).With our lifelong goal of FI, what would you recommend we do?

I'm just a 24 year old kid with no company backing me,so I really have no idea how to establish an initial professional relationship with real estate agents,contractors, etc and be taken seriously.

They hit me hard in underwriting and I ended up having to come up with a bigger down payment than they initially offered due to the current distress in the market. 

Was the initial $2300 what you spent on rehab during the two years you lived in it? 

If your initial strategy is to house-hack in the Chicago market, you may want to consider finding a neighborhood that you are comfortable living in, and close to your job.

Can I cross it off and initial?

If you finance $93500 that should put you at 55% LTV, replace your initial investment, and leave you a mortgage payment you should be able to cash flow off of. 

But they only do refinances and initial buys, so no liquidation (= getting money out of a property that doesn't have a mortgage on it...).

My initial price range for this purchase is between $120k to $150k, the market is very competitive in Omaha for this price range but I am confident I will find a deal with persistence.